Journal
ORGANIC LETTERS
Volume 21, Issue 7, Pages 2468-2472Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b00839
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Funding
- Thousand Youth Talents Plan
- NSFC [21672145, 51733007]
- Shanghai Science and Technology Committee [17JC1403700]
- Drug Innovation Major Project of the Ministry of Science and Technology of China [2018ZX09711001-005-002]
- Shanghai Sailing Program [17YF1409000]
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Asymmetric catalytic synthesis of 2,3-allenamides from hydrogen-bond-stabilized enynamides in the presence of quinine-based bifunctional squaramide organocatalysts is described. This protocol forms a variety of 2,3-allenamides in high yields and excellent stereoselectivities, in which the elaborated introduction of intramolecular H-bonds within the N,N-bidentate amide group constitutes one of the keys to this highly enantioselective transformation. The synthetic practicality of this reaction has been demonstrated by the axis-to-center chirality transfer of allenamides to furnish enantiomerically enriched building blocks.
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